Triethylamine → 4-[(5-acetyl-2-propoxybenzoyl)amino]-5-ethyl-1H-pyrazole-3-carboxamide

HRID 1837553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837553
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH3:22])=[C:14]([CH:18]=1)[C:15]([OH:17])=O)(=[O:9])[CH3:8].C(N(CC)CC)C.[NH2:30][C:31]1[C:32]([CH2:39][CH3:40])=[N:33][NH:34][C:35]=1[C:36]([NH2:38])=[O:37]>CN(C)C=O.ClCCl>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH3:22])=[C:14]([CH:18]=1)[C:15]([NH:30][C:31]1[C:35]([C:36]([NH2:38])=[O:37])=[N:34][NH:33][C:32]=1[CH2:39][CH3:40])=[O:17])(=[O:9])[CH3:8]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 226781155-Acetyl-2-n-propoxybenzoic acidHCID 178438044HCID 178438044, Verbindung

Produkt 1

HCID 226781184-[(5-acetyl-2-propoxybenzoyl)amino]-5-ethyl-1H-pyrazole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (5.45 ml, 46.4 mmol) was added to a solution of 5-acetyl-2-n-propoxy-benzoic acid (WO 9312095) (11.1 g, 30.9 mmol) in N,N-dimethylformamide (0.1 ml) and dichloromethane (200 ml) under nitrogen at room temperature. Once addition was complete the solution was stirred for 1 hour. The solution was concentrated under reduced pressure and azeotroped with toluene, and the intermediate acid chloride was dissolved in dichloromethane (200 ml). Triethylamine (10.4 ml, 46.4 mmol) was added followed by 4-amino-3-ethyl-1H-pyrazole-5-Carboxamide (WO 9849166) (7.7 g, 30.9 mmol) and the reaction was stirred at room temperature for 16 hours. The mixture was washed with 1N hydrochloric acid (2×100 ml), 10% sodium bicarbonate solution (100 ml) and brine (100 ml), dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was recrystallised from acetonitrile to afford the title compound as a crystalline solid, 14.8 g.

Aufarbeitung

  1. additionOnce addition
  2. concentrationThe solution was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. dissolutionthe intermediate acid chloride was dissolved in dichloromethane (200 ml)
  5. stirringthe reaction was stirred at room temperature for 16 hours
  6. washThe mixture was washed with 1N hydrochloric acid (2×100 ml), 10% sodium bicarbonate solution (100 ml) and brine (100 ml)
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-09c46aa1fd624eedafd9eb5d9297d030
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784185B2

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